What questions should I ask a seller first?

A first conversation with a seller is a screening exercise, not a negotiation, and the goal is to find out quickly whether a business is worth the time a full due diligence process demands. A short list of direct questions, asked early and asked plainly, does most of that work.

Why are you selling, and why now?

Retirement, burnout, a partner dispute, and a declining business can all produce a similar-looking listing, but they mean very different things for what you’re actually buying. A seller who answers this vaguely, or gives an answer that doesn’t match the business’s apparent condition, is worth a second, more pointed conversation before you go any further.

What will you actually show me, and when?

Ask directly what financial documentation the seller is prepared to share once you’ve signed a confidentiality agreement — tax filings, not just a prepared summary — and how quickly. A seller who is vague or resistant about sharing verifiable records, even after a signed NDA, is a signal to slow down rather than press forward on trust alone.

How dependent is the business on you personally?

Ask how the owner spends a typical week, and how much of the business’s relationships with customers, suppliers, and staff run through them personally rather than through documented systems. A business that runs almost entirely on the owner’s individual relationships needs a longer, more structured transition than one with systems and staff who already carry much of that load.

What happens to staff, licences, and key contracts?

• Whether key employees know a sale is happening, and whether the seller expects them to stay through a change in ownership.
• Whether any licences or permits the business needs to operate are personally held by the seller or attached to the business itself.
• Whether major customer or supplier contracts include a clause that requires consent before they can transfer to a new owner.

What transition support are you offering?

Ask plainly how many weeks or months the seller is prepared to stay involved after closing, and whether that’s already reflected in their price expectations or something you’ll need to negotiate separately. A seller who hasn’t thought about transition support at all often hasn’t thought carefully about the sale process in general, which is useful information in itself.